Acetonylchelerythrine

Details

• Internal ID: f327ba04-bdc8-4b84-b863-8d02da7064e2
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
• IUPAC Name: 1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]propan-2-one
• SMILES (Canonical): CC(=O)CC1C2=C(C=CC(=C2OC)OC)C3=C(N1C)C4=CC5=C(C=C4C=C3)OCO5
• SMILES (Isomeric): CC(=O)C[C@H]1C2=C(C=CC(=C2OC)OC)C3=C(N1C)C4=CC5=C(C=C4C=C3)OCO5
• InChI: InChI=1S/C24H23NO5/c1-13(26)9-18-22-15(7-8-19(27-3)24(22)28-4)16-6-5-14-10-20-21(30-12-29-20)11-17(14)23(16)25(18)2/h5-8,10-11,18H,9,12H2,1-4H3/t18-/m0/s1
• InChI Key: VGTQLFWIJIABSU-SFHVURJKSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.40 g/mol
• Exact Mass: 405.15762283 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.72
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 22864-92-2
• 6-Acetonyldihydrochelerythrine
• Chelerythrine acetonate
• Acetonyldihydrochelerythrine
• 13-Acetonyldihydrochelerythrine
• 13-(2-Oxopropyl)dihydrochelerythrine
• 1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]propan-2-one
• 2-Propanone,1-[(13S)-12,13-dihydro-1,2-dimethoxy-12-methyl[1,3]dioxolo[4,5]benzo[1,2-c]phenanthridin-13-yl]-
• CHEMBL250267
• DTXSID60177404
• [1,3]Benzodioxolo[5,6-c]phenanthridine, 2-propanone deriv.; 13-(2-Oxopropyl)dihydrochelerythrine; 13-Acetonyldihydrochelerythrine; Acetonylchelerythrine; Acetonyldihydrochelerythrine;
• AKOS040761194
• Chelerythrine, 13.beta.-acetonyl-12,13-dihydro-
• 1,2-Dimethoxy-12-methyl-13beta-(2-oxopropyl)-12,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridine
• 2-Propanone, 1-((13S)-12,13-dihydro-1,2-dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridin-13-yl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9600	96.00%
Caco-2	+	0.8406	84.06%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.4232	42.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9734	97.34%
P-glycoprotein inhibitior	+	0.9434	94.34%
P-glycoprotein substrate	+	0.6470	64.70%
CYP3A4 substrate	+	0.6148	61.48%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.4180	41.80%
CYP3A4 inhibition	+	0.7730	77.30%
CYP2C9 inhibition	-	0.5955	59.55%
CYP2C19 inhibition	+	0.8513	85.13%
CYP2D6 inhibition	+	0.5089	50.89%
CYP1A2 inhibition	+	0.5400	54.00%
CYP2C8 inhibition	+	0.5375	53.75%
CYP inhibitory promiscuity	+	0.7370	73.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4848	48.48%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9577	95.77%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7894	78.94%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5232	52.32%
skin sensitisation	-	0.8614	86.14%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8407	84.07%
Acute Oral Toxicity (c)	III	0.7715	77.15%
Estrogen receptor binding	+	0.9106	91.06%
Androgen receptor binding	+	0.7765	77.65%
Thyroid receptor binding	+	0.6537	65.37%
Glucocorticoid receptor binding	+	0.8957	89.57%
Aromatase binding	+	0.5729	57.29%
PPAR gamma	+	0.7715	77.15%
Honey bee toxicity	-	0.8866	88.66%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9224	92.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.27%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.69%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.56%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.17%	89.62%
CHEMBL2581	P07339	Cathepsin D	91.96%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.70%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.20%	96.00%
CHEMBL4208	P20618	Proteasome component C5	89.77%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.76%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.33%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.72%	91.11%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.80%	89.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.04%	95.56%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.46%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.36%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.55%	80.78%

Plants that contains it

• Argemone mexicana
• Cephalocroton cordofanus
• Citrus lucida
• Garcinia lucida
• Zanthoxylum ailanthoides
• Zanthoxylum integrifoliolum
• Zanthoxylum nitidum
• Zanthoxylum rhoifolium
• Zanthoxylum spinosum
• Zanthoxylum tsihanimposa
• Zanthoxylum zanthoxyloides

Cross-Links

• PubChem: 185516
• NPASS: NPC193906
• ChEMBL: CHEMBL250267
• LOTUS: LTS0167510
• wikiData: Q72434244